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10-[[[1-(Methoxymethyl)-2-[[1-(methoxymethyl)-2-[[1-(methoxymethyl)-2-carbethoxypyrrol-4-yl]carbamoyl]pyrrol-4-yl]carbamoyl]pyrrol-4-yl]carbamoyl]methoxy]-2(R,S)-camptothecin

ID: ALA73002

PubChem CID: 44311920

Max Phase: Preclinical

Molecular Formula: C45H46N8O14

Molecular Weight: 922.90

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(NC(=O)c2cc(NC(=O)c3cc(NOC(=O)COc4ccc5nc6c(cc5c4)Cn4c-6cc5c(c4=O)COC(=O)C5(O)CC)cn3COC)cn2COC)cn1COC

Standard InChI:  InChI=1S/C45H46N8O14/c1-6-45(60)32-15-34-39-26(16-53(34)42(57)31(32)20-66-44(45)59)10-25-11-30(8-9-33(25)48-39)65-21-38(54)67-49-29-14-36(51(19-29)23-62-4)41(56)46-27-12-35(50(17-27)22-61-3)40(55)47-28-13-37(43(58)64-7-2)52(18-28)24-63-5/h8-15,17-19,49,60H,6-7,16,20-24H2,1-5H3,(H,46,56)(H,47,55)

Standard InChI Key:  SWIKPKGMWWHQJE-UHFFFAOYSA-N

Molfile:  

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M  END

Associated Targets(Human)

TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-VLB (48 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 922.90Molecular Weight (Monoisotopic): 922.3133AlogP: 3.93#Rotatable Bonds: 18
Polar Surface Area: 255.96Molecular Species: NEUTRALHBA: 20HBD: 4
#RO5 Violations: 2HBA (Lipinski): 22HBD (Lipinski): 4#RO5 Violations (Lipinski): 2
CX Acidic pKa: 11.71CX Basic pKa: 3.14CX LogP: 2.79CX LogD: 2.79
Aromatic Rings: 6Heavy Atoms: 67QED Weighted: 0.05Np Likeness Score: 0.03

References

1. Zhao R, al-Said NH, Sternbach DL, Lown JW..  (1997)  Camptothecin and minor-groove binder hybrid molecules: synthesis, inhibition of topoisomerase I, and anticancer cytotoxicity in vitro.,  40  (2): [PMID:9003520] [10.1021/jm9605804]
2. Uehling, D E DE and 9 more authors.  1995-03-31  Synthesis, topoisomerase I inhibitory activity, and in vivo evaluation of 11-azacamptothecin analogs.  [PMID:7707314]
3. Luzzio, M J MJ and 9 more authors.  1995-02-03  Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I.  [PMID:7853331]
4. Wall, M E ME and 8 more authors.  1993-09-03  Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.  [PMID:8410981]
5. Lackey, K K and 10 more authors.  1996-02-02  Water soluble inhibitors of topoisomerase I: quaternary salt derivatives of camptothecin.  [PMID:8576914]
6. Saulnier, Mark G MG and 23 more authors.  2005-04-07  Discovery of a fluoroindolo[2,3-a]carbazole clinical candidate with broad spectrum antitumor activity in preclinical tumor models superior to the marketed oncology drug, CPT-11.  [PMID:15801816]
7. Sunami, Satoshi S and 5 more authors.  2009-05-28  Synthesis and biological activities of topoisomerase I inhibitors, 6-arylmethylamino analogues of edotecarin.  [PMID:19397324]

Source